


First Time

by EnsorcelledReader



Series: DirkJake NSFW OTP Challenge [7]
Category: Homestuck
Genre: Anal Sex, First Time, M/M, Mild Biting
Language: English
Status: Completed
Published: 2016-04-05
Updated: 2016-04-05
Packaged: 2018-05-31 09:36:55
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,565
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6465247
Author URL: https://archiveofourown.org/users/EnsorcelledReader/pseuds/EnsorcelledReader
Summary: <blockquote class="userstuff">
              <p>For the NSFW OTP Challenge</p>
            </blockquote>





	First Time

**Author's Note:**

> For anon from tumblr. This isn’t a particularly sexy fic. I really like awkward first time stuff and Jake being a bit of dork.

The game had been finished for two years now. You and Jake had slowly returned to a tentative friendship, apologizing for mutual fuck ups in the relationship. You both treaded carefully around each other for a good six months, trying to handle little mannerisms that you found annoying or down right unhealthy in each other, maturely. Neither of you were as mature as you would have liked to think at the time. You kept conversation civil, but whenever the other brought up a flaw there would be a good week of icy emotional distance; one that could never be proven by the other, but nonetheless was there.

It was the girls who called you out on it. Roxy mostly, although you refused to acknowledge it. Rose had to be the one to talk some sense into you, explain it to you in terms that you can understand. She’s become quite the confidante when you struggled with social norms. She explains your wrongs within the structure of a social group, rather than as an individual fault, you needed that early on; needed things to not be connected to you personally, only part of a bigger puzzle, a language that you had to learn. It helped, and you began to understand.

A year after the game ended you and Jake were on good terms again, you couldn’t deny the ache you felt for the relationship you had once had with him. You worked so hard on yourself, you knew you could be a better boyfriend; the fear of rejection and ruining what had taken so long to rebuild was enough to deter you though.

Surprisingly, it was Jake who came to you. “Now Dirk, I know you and I didn’t work out before, but….golly, I, I’m still…well…I’m still rather infatuated with you. I was wondering if you’d be willing to give it another go?” Of course, you agreed.

Your relationship with Jake the second time around was like something from a dream compared to before. It was so easy, nothing had to be forced. Sure, issues came up, but you had so many people to talk to now, to help you see your flaws and how to fix a given situation. The two of you grew closer, learning about each other’s interests and learning each other’s thought processes, understanding each other better. You learned that he loves cuddling more than making out, and that he has a gun fetish; not that you were surprised. You haven’t participated in the kink, at least for the time being, he doesn’t want you to. You confessed a desire to be dominated and your pain kink. He’s bitten you a couple of times and seems to be getting more comfortable with it.

Despite all of this, you two haven’t had sex. It was the last big gate of your physical relationship. A big step both of you were hesitant about. You know you wanted it; wanted him to pin you down and say filthy things in your ear, slapping your ass if you made too much noise. That couldn’t be expected the first time around of course, but a guy can dream.  No, when you think of your first time with Jake you expect him to be just as nervous as you, the guy isn’t exactly mister cool in emotionally intense situations. Still, you’d like to think that he’d see your own hesitation and cradle your face, kissing you reassuringly until before you know it you’re on your back and he’s on top of you. Unrealistic, you know that, less unrealistic than BDSM fantasy, but likely beyond your grasp. You’ll have to take the reins the first time through, guide him and give him direction every step of the way, he’s not the type to take charge.

 

Jake’s in your room, the two of you making out, his tongue in your mouth and hands on your torso, another thing you’ve learned about him, he’s all about that six pack. He’s tracing the muscles with his fingers, feather light touches that tickle more than arouse, yet you’re still moaning.  He’s pulled away and you’re chasing after him with your mouth, but his hands tell you to stay. Teeth nip the skin on your neck before a vicious bite makes your senses light up and you’re writhing underneath his weight and it feels so good. “Jake, Jake oh god. Yes! Ah~” You want him, you him in you so badly….It’s now or never. “Jake, fuck Jake stop.”

He pulls back in alarm, worry chasing away that precious expression that you secretly covet and wish to hide in this room, just for you. “Sorry!! Did I bite too hard? Did I do it wrong?”

“No, no. I just, damn English you really know how to work me up. I just, fuck, I want to have sex with you!” You don’t mean to say it so loud or so demandingly, the look of shock makes you want to take the words out of his ears and shove everything back in your mouth never to see the light of day and flushed down the toilet a few days later, forever leaving you. You want to bury you face in pillows, but your pride won’t let you. Your vanity insists that you sit there, stoic as ever because your internal freak out is so bad that your body has become numb to all emotion. A thick layer of repellant coats the inside of your skin, refusing to let you express even a minute amount of what you’re feeling. You weren’t built to share, even when it really matters. The fear building in your chest is becoming too much and you can feel everything slow down and speed up at the same time. Nausea is creeping in as you watch Jake’s face. He’s recovered and saying something, but your ears won’t work. “What?” you manage, but it’s weak and pathetic croak.

“Okay, I just erm, Holey Moley, Strider you sure know how to spring stuff on a guy.”

“Sorry, you don’t have to do anything, forget it. I’m an idiot, I wasn’t serious really. Please, just forget it.” Of course the internal repellant doesn’t work when you open your mouth.

“Hey now, calm down, I didn’t say it wasn’t a nice idea.”

“…really?”

“Yeah…” The two of you sit there for a few moments, your boner long gone and Jake wasn’t making any moves. The thought of prompting him crosses your mind, but you don’t want to put any more pressure on the situation.

After roughly five minutes of awkward frozen silence, a couple of half starts and awkward glances, you are afraid to move, but at the same time you want to call the whole thing off, tuck it away and pretend things never happened. Then,  Jake finally makes a move, he’s kissing you again, it’s soft and slower than before, his tongue slips back into your mouth and he’s probing while you submit and an embarrassing whine of desire and relief escapes you. He seems to gain confidence from the noise, you can feel his hand on your chest, pushing you down. He’s straddling your hips, looking at you with equal parts lust, fear, and uncertainty; just like you. One of your hands trails down one of his arms as you follow it with your eyes, flicking to look at his gaze to see him watching you. The words that come out of your mouth don’t even feel real, so stupid and so quiet “Your arms have become so muscular.”

He smirks and gives a soft floating laugh, his voice equally as gentle “Still not as strong as you.” A hand brushes stray hairs from your face “Or as nice looking.” And his lips are on you again, harder and more insistent than before, hands under your shirt, pulling it up and over your head. Breath comes in pants out of your mouth, you feel warm and delightfully dizzy as Jake sucks your neck. Embarrassing groans escape you and you finally realize that this is going to happen. Your hands claw his back trying to rip the clothes from his body, both his and your movement become frantic as every stitch of clothing is removed. He pauses and you want to complain, but you see the darkened gaze rake over your body and you shiver. He notices the involuntary movement and smiles, kisses down your torso shaky words imprint your skin with every kiss. “I-I’ve never done this before Dirk. Let me know if anything hurts or I do something wrong…okay?”

“Yeah, me too Jake. Me too.” And you feel him start to align himself with your entrance when you realize just how much Jake doesn’t know what he’s doing.  “Stop!”

“Golly, already? What did I do Dirk? I thought you wanted my tallywhacker up your caboose.”

You ignore Jake’s words and focus on their content. “Lube, Jake.” He looks at you as the information connects with common sense in his brain and he blushes a beautiful hue.

“R-right.”

“I’d prefer it if you wore a condom too.”

“Right-o, can’t believe how I could have forgotten that.” He smiles meekly finds his shorts while you’re digging in the drawer of your bedside table for lube. You consider asking Jake to prep you, more romantic and intimate that way, then you see him fumbling to get the condom from his wallet open and think better of it. Spreading the lube on your fingers you focus on working yourself open and do your best to ignore Jake struggling with the condom. He always was a butterfingers. You’re already fairly loose (you do this on a regular basis), but Jake is thick, you’ve given him enough hand jobs and blow jobs to know two fingers isn’t going to cut it. Three fingers inside yourself leaves you feeling a little full and you wonder idly why you didn’t try this before, the initial stretch is uncomfortable, but the feeling afterward is much better, especially when you scissor the fingers inside you. A groan escapes, and Jake, having successfully defeated the condom challenge, takes notice.  “What are you doing?”

A slight haze of pleasure delays your response and he’s hovering near you before you can respond. “Look at your girth dude, need some prep before I can take that.” You pull your fingers out, feeling loose enough. You also take the liberty of slicking Jake up, you highly doubt he would think to and even if he did, he probably wouldn’t use enough anyway.

You do get some enjoyment seeing the face and noise he makes as you slather the lube on, you kiss his neck before pulling away and lying once more on your back. “Alrighty then, shall we try once more?” You smile and coax him closer, and he’s balanced above you once more. He tries to guide himself in and fumbles again, but eventually you feel him push past the ring of muscle and the tip is in you. He eases himself in an exceptionally slow and gentle manner, more tender than you every thought possible. Kisses are trailing on your face, when did you scrunch up your face and eyes? And when did your heartbeat become so loud in your ears? He’s talking to you, “Come on Dirk, I need you to talk to me. I’m not hurting you am I?” Everything has frozen and you have to force yourself to relax and open your eyes, he’s worried. You must look scared because he’s brought a hand to you face, his eyes search yours as his thumb caresses your cheek. “We can stop.”

You shake your head, “Just give me a minute.” You realize the stretch has broken past uncomfortable and is teetering on the edge of pain. You try to relax, but some part of you is panicking, what if this was a bad idea, what if this doesn’t work? What if you take too long…and…and….the hand on your face as moved to the side of your torso, circles traced just above the hip, he’s whispering the sweetest words in your ear.

“Shh, it’s okay. Take your time. I’m here. I’m here Dirk. If it’s too much we can stop, it’s okay.” And you feel yourself relax, the near pain dissolving back into a mild discomfort.

You let breath fill your lungs and his words reassure you before saying, “You can move” in a small voice.  He’s pushing into you again and you pay more attention this time, stopping him when the stretch is just shy of your limits. It’s a slow process, but he eventually sheathes himself completely in you. You both let out small nervous laughs and he says “we did it” like it’s some miracle and you kiss him because fuck if that didn’t make you love him that much more.

After one last moment to adjust, you give him the go ahead, and he moves inside you. Shallow, gentle thrusts as he watches you and moans at the feeling. It takes you a little longer to join him in carnal delight, but you get there. He’s not hitting your prostate, but it feels good regardless. You let out broken whimpers of his name. He kisses you in response and his speed is picking up.

He lasts all of two minutes before coming inside you. The sensation of his hot release into the condom makes you shudder. Watching his face as he rides his orgasm pleases you in a way you can’t describe, somewhere between arousal and love, affection comes to mind, but isn’t powerful enough to express it. When he comes out of the haze you can see humiliation shroud his face. “I-I’m sorry. You didn’t-” He starts to pull out of you and you grasp his arm.

“Can you jerk me off like this?” You feel so pleasantly full and warm, you want to climax with him inside of you, even if you couldn’t climax with him. The shame ebbs away from his face, he smiles; never really expected Jake to last long anyway, never had stamina. You didn’t care though and you still don’t. He grasps your dick in his hand and you may exaggerate your response a little, to reassure him that he is a great source of pleasure for you, that he didn’t fail. Any acting you do melts into actual experience and you’re calling his name as you peak.

A satisfying fuzziness clings to the periphery of your senses as reality creeps back into your perception. He’s pulled out of you and is kissing your shoulder, the condom already discarded, his hand caressing your stomach, no, cleaning it. You tilt his chin and pucker your lips, he takes the invitation and kisses you sweetly before pressing your foreheads together. Neither of you say anything as you feel a blissful sleepiness tug at the back of your skull. “Cuddles.” The last effort you’ll make to speak tonight. You’re pretty sure Jake yawns as he pulls a blanket up around both of you and you both settle into the communal warmth.

You’re not sure “I love you” leaves your lips in the final moments of lucidity. As the last grains of sand funnel into the hourglass of night, you vow to tell him in the morning, and every day after that.


End file.
